CA2030396C - Derives 5-[1-(imidazol)methyl]-3,3-(disubstituant)-2 (3h)furanone - Google Patents

Derives 5-[1-(imidazol)methyl]-3,3-(disubstituant)-2 (3h)furanone

Info

Publication number: CA2030396C
Authority: CA; Canada
Prior art keywords: compound; methyl; diphenyl; furanone; dihydro
Prior art date: 1990-05-08
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

CA002030396A

Other languages

English (en)

Other versions

CA2030396A1 (fr

Inventor

Ciro Jerry Spagnuolo

Carl Kaiser

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Aventis Pharmaceuticals Inc

Original Assignee

Hoechst Marion Roussel Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-05-08

Filing date

1990-11-20

Publication date

1997-02-25

1990-11-20 Application filed by Hoechst Marion Roussel Inc filed Critical Hoechst Marion Roussel Inc

1991-11-09 Publication of CA2030396A1 publication Critical patent/CA2030396A1/fr

1997-02-25 Application granted granted Critical

1997-02-25 Publication of CA2030396C publication Critical patent/CA2030396C/fr

2010-11-20 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims description 99
150000001875 compounds Chemical class 0.000 claims abstract description 67
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
125000000217 alkyl group Chemical group 0.000 claims abstract description 26
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 18
239000001257 hydrogen Substances 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 13
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
150000002367 halogens Chemical group 0.000 claims abstract description 10
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
208000000693 Neurogenic Urinary Bladder Diseases 0.000 claims abstract description 6
125000002541 furyl group Chemical group 0.000 claims abstract description 6
150000002431 hydrogen Chemical class 0.000 claims abstract description 6
125000001544 thienyl group Chemical group 0.000 claims abstract description 5
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical group O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims abstract description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract 2
125000002843 carboxylic acid group Chemical group 0.000 claims abstract 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 claims description 24
239000000812 cholinergic antagonist Substances 0.000 claims description 11
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 8
229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
208000035475 disorder Diseases 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
229940124575 antispasmodic agent Drugs 0.000 claims description 3
206010009887 colitis Diseases 0.000 claims description 3
208000002551 irritable bowel syndrome Diseases 0.000 claims description 3
230000001148 spastic effect Effects 0.000 claims description 3
206010009900 Colitis ulcerative Diseases 0.000 claims description 2
206010012735 Diarrhoea Diseases 0.000 claims description 2
201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
208000007784 diverticulitis Diseases 0.000 claims description 2
BVPWJMCABCPUQY-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-N-[1-(phenylmethyl)-4-piperidinyl]benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NC1CCN(CC=2C=CC=CC=2)CC1 BVPWJMCABCPUQY-UHFFFAOYSA-N 0.000 claims 1
MVYHVKRKPJORKK-UHFFFAOYSA-M 5-(6,7-dihydro-5h-pyrrolo[1,2-a]imidazol-4-ium-1-ylmethyl)-3,3-diphenyloxolan-2-one;chloride Chemical compound [Cl-].O=C1OC(C[N+]2=C3CCCN3C=C2)CC1(C=1C=CC=CC=1)C1=CC=CC=C1 MVYHVKRKPJORKK-UHFFFAOYSA-M 0.000 claims 1
206010020772 Hypertension Diseases 0.000 claims 1
239000002637 mydriatic agent Substances 0.000 claims 1
239000002731 stomach secretion inhibitor Substances 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 45
239000002253 acid Chemical group 0.000 abstract description 7
150000002241 furanones Chemical class 0.000 abstract description 4
230000001078 anti-cholinergic effect Effects 0.000 abstract description 3
125000001424 substituent group Chemical group 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 90
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
239000000243 solution Substances 0.000 description 56
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 52
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 51
229910001868 water Inorganic materials 0.000 description 43
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 36
-1 e.g. Natural products 0.000 description 36
239000007787 solid Substances 0.000 description 35
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 32
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
238000005160 1H NMR spectroscopy Methods 0.000 description 22
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
239000000377 silicon dioxide Substances 0.000 description 20
229910052786 argon Inorganic materials 0.000 description 18
239000007788 liquid Substances 0.000 description 18
210000001519 tissue Anatomy 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000010410 layer Substances 0.000 description 15
239000000047 product Substances 0.000 description 15
239000012267 brine Substances 0.000 description 14
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
238000004809 thin layer chromatography Methods 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 12
238000002360 preparation method Methods 0.000 description 12
229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
238000005481 NMR spectroscopy Methods 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000012044 organic layer Substances 0.000 description 9
235000017557 sodium bicarbonate Nutrition 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
229940124630 bronchodilator Drugs 0.000 description 8
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 8
229960004484 carbachol Drugs 0.000 description 8
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
229910000041 hydrogen chloride Inorganic materials 0.000 description 8
210000003405 ileum Anatomy 0.000 description 8
210000003205 muscle Anatomy 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
230000003287 optical effect Effects 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
239000005557 antagonist Substances 0.000 description 5
230000002921 anti-spasmodic effect Effects 0.000 description 5
230000008602 contraction Effects 0.000 description 5
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 5
UTSOXZIZVGUTCF-UHFFFAOYSA-N hydrate;hydroiodide Chemical compound O.I UTSOXZIZVGUTCF-UHFFFAOYSA-N 0.000 description 5
239000003149 muscarinic antagonist Substances 0.000 description 5
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 description 4
IRQJWIUKHLVISG-UHFFFAOYSA-N 3,3-diphenyloxolan-2-one Chemical compound O=C1OCCC1(C=1C=CC=CC=1)C1=CC=CC=C1 IRQJWIUKHLVISG-UHFFFAOYSA-N 0.000 description 4
108010009685 Cholinergic Receptors Proteins 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
102000034337 acetylcholine receptors Human genes 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000003814 drug Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
150000002460 imidazoles Chemical class 0.000 description 4
239000000463 material Substances 0.000 description 4
238000000034 method Methods 0.000 description 4
210000004877 mucosa Anatomy 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000012258 stirred mixture Substances 0.000 description 4
239000011550 stock solution Substances 0.000 description 4
238000012360 testing method Methods 0.000 description 4
OEQULLJAMWIGFS-UHFFFAOYSA-N (5-oxo-4,4-diphenyloxolan-2-yl)methyl trifluoromethanesulfonate Chemical compound O=C1OC(COS(=O)(=O)C(F)(F)F)CC1(C=1C=CC=CC=1)C1=CC=CC=C1 OEQULLJAMWIGFS-UHFFFAOYSA-N 0.000 description 3
BLRSCYRFTSBWIH-UHFFFAOYSA-N 2,2-diphenylpent-4-enoic acid Chemical compound C=1C=CC=CC=1C(CC=C)(C(=O)O)C1=CC=CC=C1 BLRSCYRFTSBWIH-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 3
FUOZJYASZOSONT-UHFFFAOYSA-N 2-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=NC=CN1 FUOZJYASZOSONT-UHFFFAOYSA-N 0.000 description 3
MBGYGMYTTAWZRC-UHFFFAOYSA-N 3,3-diphenyloxolan-2-one hydrochloride Chemical compound Cl.O=C1OCCC1(c1ccccc1)c1ccccc1 MBGYGMYTTAWZRC-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
241000700198 Cavia Species 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
230000001262 anti-secretory effect Effects 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000000969 carrier Substances 0.000 description 3
230000001186 cumulative effect Effects 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000012259 ether extract Substances 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000012458 free base Substances 0.000 description 3
239000011521 glass Substances 0.000 description 3
230000003551 muscarinic effect Effects 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
230000004044 response Effects 0.000 description 3
238000013207 serial dilution Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
235000017550 sodium carbonate Nutrition 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
150000008648 triflates Chemical class 0.000 description 3
BBKBPYFNBFEICG-RXMQYKEDSA-N (4s)-4-(iodomethyl)-2,2-dimethyl-1,3-dioxolane Chemical compound CC1(C)OC[C@@H](CI)O1 BBKBPYFNBFEICG-RXMQYKEDSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 2
QKWWDTYDYOFRJL-UHFFFAOYSA-N 2,2-dimethoxyethanamine Chemical compound COC(CN)OC QKWWDTYDYOFRJL-UHFFFAOYSA-N 0.000 description 2
RFXJLECGYGFJCI-UHFFFAOYSA-N 2-(2-methylpropyl)-1h-imidazole Chemical compound CC(C)CC1=NC=CN1 RFXJLECGYGFJCI-UHFFFAOYSA-N 0.000 description 2
OLOFOLZWOJTRCH-UHFFFAOYSA-N 2-(3-chloropropyl)-1h-imidazole Chemical compound ClCCCC1=NC=CN1 OLOFOLZWOJTRCH-UHFFFAOYSA-N 0.000 description 2
XHOIMCPVMWYING-UHFFFAOYSA-N 2-(4-chlorobutyl)-1h-imidazole Chemical compound ClCCCCC1=NC=CN1 XHOIMCPVMWYING-UHFFFAOYSA-N 0.000 description 2
NAPDOWNULRULLI-UHFFFAOYSA-N 2-benzyl-1h-imidazole Chemical compound C=1C=CC=CC=1CC1=NC=CN1 NAPDOWNULRULLI-UHFFFAOYSA-N 0.000 description 2
PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 2
YOCJROFWSPBGHT-GOSISDBHSA-N 4-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-diphenylbutanoic acid Chemical compound O1C(C)(C)OC[C@H]1CCC(C(O)=O)(C=1C=CC=CC=1)C1=CC=CC=C1 YOCJROFWSPBGHT-GOSISDBHSA-N 0.000 description 2
ZZNFCXDBEFYYQN-UHFFFAOYSA-N 4-methyl-2,2-diphenylpent-4-enoic acid Chemical compound C=1C=CC=CC=1C(C(O)=O)(CC(=C)C)C1=CC=CC=C1 ZZNFCXDBEFYYQN-UHFFFAOYSA-N 0.000 description 2
LFNWFGDMNXCZMD-UHFFFAOYSA-N 5-(bromomethyl)-3,3-diphenyloxolan-2-one Chemical compound O=C1OC(CBr)CC1(C=1C=CC=CC=1)C1=CC=CC=C1 LFNWFGDMNXCZMD-UHFFFAOYSA-N 0.000 description 2
ZOYPNYUYSXBWHK-UHFFFAOYSA-N 5-methyl-3,3-diphenylfuran-2-one Chemical compound O=C1OC(C)=CC1(C=1C=CC=CC=1)C1=CC=CC=C1 ZOYPNYUYSXBWHK-UHFFFAOYSA-N 0.000 description 2
PJHQGRVJYVMEKL-UHFFFAOYSA-N 5-methylidene-3,3-diphenyloxolan-2-one Chemical compound O=C1OC(=C)CC1(C=1C=CC=CC=1)C1=CC=CC=C1 PJHQGRVJYVMEKL-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229930003347 Atropine Natural products 0.000 description 2
206010006458 Bronchitis chronic Diseases 0.000 description 2
206010006482 Bronchospasm Diseases 0.000 description 2
244000025254 Cannabis sativa Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
JKRBPKCHHLUJJX-UHFFFAOYSA-N Cl.O=C1CC=CO1 Chemical compound Cl.O=C1CC=CO1 JKRBPKCHHLUJJX-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
208000008469 Peptic Ulcer Diseases 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
RNVYQYLELCKWAN-YFKPBYRVSA-N [(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol Chemical compound CC1(C)OC[C@H](CO)O1 RNVYQYLELCKWAN-YFKPBYRVSA-N 0.000 description 2
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
229960004373 acetylcholine Drugs 0.000 description 2
230000009471 action Effects 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
239000000556 agonist Substances 0.000 description 2
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
230000008485 antagonism Effects 0.000 description 2
230000001022 anti-muscarinic effect Effects 0.000 description 2
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229920001277 pectin Polymers 0.000 description 1
239000008188 pellet Substances 0.000 description 1
210000003200 peritoneal cavity Anatomy 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
229960001416 pilocarpine Drugs 0.000 description 1
JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
230000001242 postsynaptic effect Effects 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
229960005253 procyclidine Drugs 0.000 description 1
208000002815 pulmonary hypertension Diseases 0.000 description 1
PMDSRSSLWQASHS-UHFFFAOYSA-N pyridin-1-ium;chloride;hydrate Chemical compound O.Cl.C1=CC=NC=C1 PMDSRSSLWQASHS-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
230000007480 spreading Effects 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
229960004791 tropicamide Drugs 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Ophthalmology & Optometry (AREA)
Pulmonology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA002030396A 1990-05-08 1990-11-20 Derives 5-[1-(imidazol)methyl]-3,3-(disubstituant)-2 (3h)furanone Expired - Lifetime CA2030396C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US520,505		1990-05-08
US07/520,505 US5039691A (en)	1989-06-08	1990-05-08	5-(1-(imidazol)methyl)-3,3-disubstituted-2(3H)furanone derivatives

Publications (2)

Publication Number	Publication Date
CA2030396A1 CA2030396A1 (fr)	1991-11-09
CA2030396C true CA2030396C (fr)	1997-02-25

Family

ID=24072888

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002030396A Expired - Lifetime CA2030396C (fr)	1990-05-08	1990-11-20	Derives 5-[1-(imidazol)methyl]-3,3-(disubstituant)-2 (3h)furanone

Country Status (5)

Country	Link
US (1)	US5039691A (fr)
EP (1)	EP0455909A3 (fr)
JP (1)	JPH0717635B2 (fr)
AU (1)	AU634602B2 (fr)
CA (1)	CA2030396C (fr)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6214801B1 (en) *	1996-01-23	2001-04-10	The Regents Of The University Of Michigan	Imidazo[1,2-a]pyridine C-nucleosides as antiviral agents
CA2472746A1 (fr) *	2002-01-14	2003-07-24	Boehringer Ingelheim Pharmaceuticals, Inc.	Mimetiques de glucocorticoides, procedes de fabrication, preparations pharmaceutiques renfermant ces mimetiques et utilisations
UA80120C2 (en) *	2002-03-26	2007-08-27	Boehringer Ingelheim Pharma	Glucocorticoid mimetics, pharmaceutical composition based thereon
CA2477764A1 (fr) *	2002-03-26	2003-10-09	Boehringer Ingelheim Pharmaceuticals, Inc.	Mimetiques du glucocorticoide, procedes de fabrication de ces mimetiques, compositions pharmaceutiques et leurs utilisations
US7186864B2 (en)	2002-05-29	2007-03-06	Boehringer Ingelheim Pharmaceuticals, Inc.	Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof
US7074806B2 (en) *	2002-06-06	2006-07-11	Boehringer Ingelheim Pharmaceuticals, Inc.	Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof
CA2496175A1 (fr) *	2002-08-21	2004-03-04	Boehringer Ingelheim Pharmaceuticals, Inc.	Composes mimetiques de glucocorticoide, leurs procedes de fabrication, compositions pharmaceutiques, et leurs utilisations
EA011095B1 (ru) *	2002-08-29	2008-12-30	Бёрингер Ингельхайм Фармасьютиклз, Инк.	Производные 3-(сульфонамидоэтил)индола, предназначенные для использования в качестве миметиков глюкокортикоидов при лечении воспалительных, аллергических и пролиферативных заболеваний
CA2512257A1 (fr) *	2003-01-03	2004-07-29	Boehringer Ingelheim Pharmaceuticals, Inc.	Derives de 1-propanol et 1-propylamine et leur utilisation en tant que ligands de glucocorticoide
US20040224992A1 (en) *	2003-02-27	2004-11-11	Boehringer Ingelheim Pharmaceuticals, Inc.	Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof
UY28526A1 (es)	2003-09-24	2005-04-29	Boehringer Ingelheim Pharma	Miméticos de glucocorticoides, métodos de preparación composiciones farmacéuticas y usos de los mismos
ES2290769T3 (es) *	2003-10-16	2008-02-16	Boehringer Ingelheim Pharmaceuticals Inc.	Sintesis estereoselectiva de ciertos alcoholes substituidos con trifluormetilo.
US7795272B2 (en) *	2004-03-13	2010-09-14	Boehringer Ingelheim Pharmaceutical, Inc.	Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof
PE20060776A1 (es) *	2004-12-27	2006-09-26	Boehringer Ingelheim Pharma	Mimeticos de glucocorticoides, metodos para prepararlos y composiciones farmaceuticas
AU2007292155B2 (en)	2006-09-05	2012-11-01	Kyowa Kirin Co., Ltd.	Imidazole derivative
EP2102170A2 (fr) *	2006-12-06	2009-09-23	Boehringer Ingelheim International GmbH	Substances mimétiques de glucocorticoïde, procédés de préparation de celles-ci, compositions pharmaceutiques et utilisations de celles-ci
CA2726449A1 (fr) *	2008-06-06	2009-12-10	Boehringer Ingelheim International Gmbh	Mimetiques de glucocorticoides, leurs procedes de fabrication, des compositions pharmaceutiques et leurs utilisations
CN105712934A (zh) *	2014-12-04	2016-06-29	黄冈银河阿迪药业有限公司	1-甲基-2-乙基咪唑的制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL7005112A (en) *	1969-04-14	1970-10-16		Broad spectrum imidazopyridines
DE2232132A1 (de) *	1972-06-30	1974-01-10	Boehringer Sohn Ingelheim	Neue substituierte 2-phenylaminoimidazoline-(2), deren saeureadditionssalze sowie verfahren zu deren herstellung
US4384879A (en) *	1980-07-15	1983-05-24	Ciba-Geigy Corporation	4-(1H-Azolylmethyl)-1,3-dioxolan-5-one derivatives, production thereof and use thereof as growth regulators and/or microbicides
DE3402166A1 (de) *	1984-01-23	1985-07-25	Hoechst Ag, 6230 Frankfurt	Azolyl-aryl-alkanol-derivate, verfahren zu ihrer herstellung und ihre verwendung

1990
- 1990-05-08 US US07/520,505 patent/US5039691A/en not_active Expired - Lifetime
- 1990-11-20 EP EP19900312633 patent/EP0455909A3/en not_active Ceased
- 1990-11-20 CA CA002030396A patent/CA2030396C/fr not_active Expired - Lifetime
- 1990-11-23 AU AU66957/90A patent/AU634602B2/en not_active Expired
- 1990-12-14 JP JP2410508A patent/JPH0717635B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
AU634602B2 (en)	1993-02-25
AU6695790A (en)	1991-11-14
JPH0717635B2 (ja)	1995-03-01
CA2030396A1 (fr)	1991-11-09
US5039691A (en)	1991-08-13
EP0455909A2 (fr)	1991-11-13
JPH04103581A (ja)	1992-04-06
EP0455909A3 (en)	1992-05-27

Legal Events

Date	Code	Title	Description
1992-02-03	EEER	Examination request
2010-11-20	MKEX	Expiry

Publication	Publication Date	Title
CA2030396C (fr)	1997-02-25	Derives 5-[1-(imidazol)methyl]-3,3-(disubstituant)-2 (3h)furanone
US6841684B2 (en)	2005-01-11	Imidiazoles having reduced side effects
EP0166533B1 (fr)	1990-04-11	Quinolones comme agents inotropes
US20100324084A1 (en)	2010-12-23	Urea derivatives of tropane, their preparation and their therapeutic application
US6103747A (en)	2000-08-15	Imidazole derivatives and process for preparing the same
EP0266730B1 (fr)	1994-08-10	Esters de l'hexahydro-8-hydroxy-2,6-méthano-2H-quinolizin-3-(4H)-one et composés apparentés
HUT58073A (en)	1992-01-28	Process for producing new benzopyran derivatives and pharmaceutical compositions comprising same
JPS6388179A (ja)	1988-04-19	トランス−６−〔２−（ｎ−ヘテロアリ−ル−３，５−ジ置換ピラゾ−ル−４−イル）エチル〕−またはエテニル〕テトラヒドロ−４−ヒドロキシピラン−２−オン
JPH11508267A (ja)	1999-07-21	ピラゾール化合物および医薬組成物
JP3120857B2 (ja)	2000-12-25	新規な縮合複素環化合物とこれを用いた抗喘息剤
Kaiser et al.	1992	Synthesis and antimuscarinic properties of some N-substituted 5-(aminomethyl)-3, 3-diphenyl-2 (3H)-furanones
TW424087B (en)	2001-03-01	1,3-dihydro-1-(phenylalkenyl)-2H-imidazol-2-one derivatives
DK166584B1 (da)	1993-06-14	Substituerede 4-benzyl-1h-imidazoler, fremgangsmaade til deres fremstilling samt farmaceutiske praeparater indeholdende dem
US5064850A (en)	1991-11-12	Dihydro-3,3-diphenyl-5-(1H-pyrazol-1-ylmethyl-2(3H)-furanone and dihydro-5-((substituted-1H-pyrazol-1-yl)methyl)-3,3-diphenyl-2(3H)-furanone derivatives
FI61489B (fi)	1982-04-30	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 6-arylpyrrolo-(1,2-a)imidatzolderivat
US4968698A (en)	1990-11-06	Nitrogen containing heterocyclic compounds
US4859691A (en)	1989-08-22	Certain 1,2-benzisoxazole derivatives
EP0133248A2 (fr)	1985-02-20	Dérivés du 1,2,4-Triazol-1-yle
US4997843A (en)	1991-03-05	2,4-disubstituted derivatives of tetrahydrofuran useful for the treatment of PAF mediated illnesses
NZ266541A (en)	1997-11-24	Imidazole derivatives, intermediate compounds and pharmaceutical compositions
JP2000501072A (ja)	2000-02-02	イミダゾール−ｎ−ベンジルジオキソールの新誘導体、それらの製造方法、それらの薬剤としての用途、製薬組成物及び新規な用途
US5753678A (en)	1998-05-19	Heterocyclic compounds
US5102900A (en)	1992-04-07	Imidazoles useful as antiatherosclerotic agents
US9464058B2 (en)	2016-10-11	Imidazolylketone derivatives
CA1292736C (fr)	1991-12-03	Derives d'ergoline et leurs sels additifs acides